US7329630B2 - Stabilizers and anti-fade agents for use in infrared sensitive leuco dye compositions - Google Patents
Stabilizers and anti-fade agents for use in infrared sensitive leuco dye compositions Download PDFInfo
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- US7329630B2 US7329630B2 US10/655,684 US65568403A US7329630B2 US 7329630 B2 US7329630 B2 US 7329630B2 US 65568403 A US65568403 A US 65568403A US 7329630 B2 US7329630 B2 US 7329630B2
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- infrared absorber
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- 239000003381 stabilizer Substances 0.000 title claims abstract description 67
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Classifications
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Definitions
- the present invention relates generally to color forming compositions. More particularly, the present invention relates to components used to enhance the light stability and long term appearance of such compositions.
- compositions which produce a color change upon exposure to light or heat are of great interest in producing images on a variety of substrates.
- Optical disks represent a significant percentage of the market for data storage of software as well as of photographic, video, and/or audio data.
- optical disks typically have data patterns embedded thereon that can be read from and/or written to one side of the disk, and a graphic display printed on the other side of the disk.
- printed patterns or graphic display information can be provided on the non-data side of the disk.
- the patterns or graphic display can be both decorative and provide pertinent information about the data content of the disk.
- commercial labeling has been routinely accomplished using screen-printing methods. While this method can provide a wide variety of label content, it tends to cost ineffective for production of less than about 400 customized disks because of the fixed costs associated with preparing a stencil or combination of stencils and printing the desired pattern or graphic display.
- leuco dye-containing compositions have been investigated for use on optical disks and other substrates.
- Leuco dye compositions thus far investigated often include a leuco dye along with an optional activator and an infrared absorber.
- many of these compositions are insufficiently stable under light exposure, and are not durable enough for practical use. Over a period of a short time, exposure to sunlight or fluorescent lights can reduce activity and absorbance of the infrared absorbers, thus reducing the quality of leuco dye development.
- the leuco dye and/or other components have a tendency to cause browning during exposure to ambient light sources and/or UV light used during curing steps. For this and other reasons, the need still exists for leuco dye compositions which have improved stability, and which have improved image forming and developing characteristics.
- a color forming composition can include a leuco dye, an infrared absorber, and at least one of a stabilizer and an anti-fade agent.
- the stabilizers can include chroman, thiolane-nickel complexes, spiroindanes, while suitable anti-fade agents can include vitamin E, vitamin E analogs, chroman, astaxanthin, ascorbic acid, carotene, and mixtures thereof.
- the term “color forming composition” typically includes a leuco dye, an infrared absorber, and at least one of a stabilizer and an anti-fade agent. These components can work together upon exposure to infrared radiation to reduce the leuco dye to produce a dye having color or a change in color.
- the term “color” or “colored” can refer to change in visible absorbance that occurs upon development, including development to black, white, or traditional colors.
- An undeveloped leuco dye can be colorless or may have some color which changes upon development to a different color.
- developer refers to an interaction or reaction which reduces the leuco dye to produce a visible change in color through reduction to the corresponding colored leuco dye.
- infrared absorber refers generally to an infrared radiation sensitive agent that can generate heat or otherwise transfer energy to surrounding molecules upon exposure to infrared radiation.
- Infrared radiation includes near infrared radiation in the range of from about 700 nm to about 40 ⁇ m, although about 700 nm to about 1200 nm is common for most near infrared applications.
- an infrared absorber can be present in sufficient quantity so as to produce heat sufficient to at least partially develop the leuco dye in accordance with embodiments of the present invention.
- thermal contact refers to the spatial relationship between an absorber and a color forming composition.
- the heat generated by the absorber should be sufficient to cause the leuco dye of the color forming composition to darken, or change or become colored, though a chemical reaction.
- Thermal contact can include close proximity between an absorber and a color forming composition, which allows for heat transfer from the absorber toward the leuco dye and/or activator. Thermal contact can also include actual contact between an absorber and leuco dye, such as in immediately adjacent layers, or in an admixture including both constituents.
- optical proximity refers to the spatial relationship of the stabilizer with respect to the infrared absorber. Specifically, in order for the stabilizer to effectively protect the infrared absorber from significant decrease in activity, the stabilizer can be admixed with or overcoated with respect to the infrared absorber.
- optical density refers to the logarithm of the reciprocal of transmittance, where transmittance is the radio of transmitted power to incident power.
- spin-coatable composition includes a liquid carrier having various components dissolved or dispersed therein.
- the spin-coatable composition can comprise a leuco dye and an infrared absorber in a common liquid carrier.
- fewer components can be present in a liquid carrier forming the spin-coatable composition.
- the leuco dye and an optional activator can be spin-coatable and applied to a substrate and then an infrared absorber can be formed in a separate layer which can be applied by spraying, screen-printing, or other methods which do not require spin-coatability.
- Color forming compositions can be spin-coatable in one embodiment, or can be configured for other application methods as well, e.g., printing such has offset, ink-jet, gravure, roller coating, screen printing or other application methods known to those skilled in the art.
- compositions of the present invention can be optimized for development using 780 nm laser light in which substantially all of the color forming composition exposed to the infrared radiation is developed in less than a predetermined period of time, e.g., 100 ⁇ sec.
- a predetermined period of time e.g. 100 ⁇ sec.
- “optimized” does not necessarily indicate that the color forming composition is developed most rapidly at a specific wavelength, but rather that the composition can be developed within a specified time frame using a given infrared radiation source.
- An optimized composition would also indicate an ambient light stability over extended periods of time, i.e. several months to years.
- optical disk is meant to encompass audio, video, multi-media, and/or software disks that are machine readable in a CD and/or DVD drive, or the like.
- optical disk formats include writeable, recordable, and rewriteable disks such as DVD, DVD-R, DVD-RW, DVD+R, DVD+RW, DVD-RAM, CD, CD-ROM, CD-R, CD-RW, and the like.
- Other like formats may also be included, such as similar formats and formats to be developed in the future.
- graphic display can include any visible character or image found on an optical disk. Typically, the graphic display is found prominently on one side of the optical disk, though this is not always the case.
- data is typically used with respect to the present disclosure to include the non-graphic information contained on the optical disk that is digitally or otherwise embedded therein.
- Data can include audio information, video information, photographic information, software information, and the like.
- weight percent values are measured relative to a dry basis, thus excluding the liquid carrier.
- values of “wt %,” “% by weight,” or “weight percent” refer to the compositions that will be present in the color forming composition excluding any carrier, such as after drying or curing, as in case of UV (ultraviolet) or EB (electron beam) curable formulations, on a substrate.
- a size range of about 1 ⁇ m to about 200 ⁇ m should be interpreted to include not only the explicitly recited limits of 1 ⁇ m to about 200 ⁇ m, but also to include individual sizes such as 2 ⁇ m, 3 ⁇ m, 4 ⁇ m, and sub-ranges such as 10 ⁇ m to 50 ⁇ m, 20 ⁇ m to 100 ⁇ m, etc.
- a color forming composition can include a leuco dye, an infrared absorber admixed with or in thermal contact with the leuco dye.
- the color forming compositions of the present invention can further include at least one of a stabilizer and an anti-fade agent, each component having beneficial effects on the long-term stability and color forming characteristics of the composition.
- the stabilizer can be configured for stabilizing the infrared absorber and the anti-fade agent can be configured for inhibiting oxidation, or browning due to other processes, of the leuco dye.
- the present invention provides improved color forming compositions on optical disk substrates, including various specific stabilizers and anti-fade agents suitable for use with certain infrared absorbers and leuco dyes.
- the infrared absorber and leuco dye Upon application of infrared energy, the infrared absorber and leuco dye are heated sufficiently to cause chemical change of the leuco dye to form the colored form of the leuco dye.
- Specific leuco dyes, infrared absorbers, stabilizers, and anti-fade agents each affect the long-term stability and development properties of the color forming composition and are discussed in more detail below.
- the color forming composition of the present invention can include a wide variety of leuco dyes.
- Suitable leuco dyes include, but are not limited to, fluorans, phthalides, amino-triarylmethanes, aminoxanthenes, aminothioxanthenes, amino-9,10-dihydro-acridines, aminophenoxazines, aminophenothiazines, aminodihydro-phenazines, aminodiphenylmethanes, aminohydrocinnamic acids (cyanoethanes, leuco methines) and corresponding esters, 2(p-hydroxyphenyl)-4,5-diphenylimidazoles, indanones, leuco indamines, hydrozines, leuco indigoid dyes, amino-2,3-dihydroanthraquinones, tetrahalo-p,p′-biphenols, 2(p-hydroxyphenyl)-4,5-diphenylimidazo
- the leuco dye can be a fluoran, phthalide, aminotriarylmethane, or mixture thereof.
- suitable fluoran based leuco dyes include 3-diethylamino-6-methyl-7-anilinofluorane, 3-(N-ethyl-p-toluidino)-6-methyl-7-anilinofluorane, 3-(N-ethyl-N-isoamylamino)-6-methyl-7-methyl-7-anilinofluorane, 3-diethylamino-6-methyl-7-(o,p-dimethylanilino)fluorane, 3-pyrrolidino-6-methyl-7-anilinofluorane, 3-piperidino-6-methyl-7-anilinofluorane, 3-(N-cyclohexyl-N-methylamino)-6-methyl-7-anilinofluorane, 3-diethylamino-7-(m
- Suitable aminotriarylmethane leuco dyes can also be used in the present invention such as tris(N,N-dimethylaminophenyl) methane (LCV); tris(N,N-diethylaminophenyl) methane(LECV); tris(N,N-di-n-propylaminophenyl) methane (LPCV); tris(N,N-di-n-butylaminophenyl) methane (LBCV); bis(4-diethylaminophenyl)-(4-diethylamino-2-methyl-phenyl) methane (LV-1); bis(4-diethylamino-2-methylphenyl)-(4-diethylamino-phenyl) methane (LV-2); tris(4-diethylamino-2-methylphenyl) methane (LV-3); bis(4-diethylamino-2-methylphenyl)(3,4-dime
- leuco dyes can also be used in connection with the present invention and are known to those skilled in the art. A more detailed discussion of some of these types of leuco dyes may be found in U.S. Pat. Nos. 3,658,543 and 6,251,571, each of which are hereby incorporated by reference in their entireties. Additional examples and methods of forming such compounds can be found in Chemistry and Applications of Leuco Dyes, Muthyala Ramaiha, ed., Plenum Press, New York, London; ISBN: 0-306-45459-9, which is hereby incorporated by reference.
- the leuco dyes can be present in color forming compositions of the present invention at from about 1 wt % to about 40 wt %. Although amounts outside this range can be successfully used, depending on the other components of the composition, amounts of from about 5 wt % to about 20 wt % frequently provide adequate results.
- An infrared radiation absorber can be included in the color forming composition as a component which can be used to optimize development of the color forming composition at a predetermined speed and/or wavelength.
- the infrared absorber can be applied as a separate layer which can be optionally spin-coatable or screen-printable, or can be applied in a common liquid carrier with the leuco dye.
- the infrared absorber can act as an energy antenna, providing heat to surrounding areas upon interaction with an energy source. As a predetermined amount of heat can be provided by the infrared absorber, matching of the infrared wavelength and intensity to the particular absorber used can be carried out to optimize the system.
- Various absorbers will act as an antenna to absorb electromagnetic radiation of specific wavelengths and ranges.
- laser light having infrared wavelengths from about 600 nm to about 1200 nm. Therefore, the present invention can provide color forming compositions optimized for use in devices that emit wavelengths within this range.
- Typical commercial IR lasers found in common CD and DVD equipment provide energy at a wavelength of about 650 nm, 780 nm, and 900 nm, while other commercial imaging lasers such as GaAs lasers can operate at about 830 nm.
- the compositions of the present invention using appropriate infrared radiation absorbers can be used in equipment that is already commonly available on the market.
- infrared wavelengths in the near infrared range having wavelengths from about 760 nm to about 1200 nm can be used in accordance with the present invention, and in one aspect, can be from about 760 nm to about 850 nm. In another more specific aspect, infrared radiation having a wavelength of from about 760 nm to about 800 nm can be used.
- the absorber can be configured to be in a heat-conductive relationship with the leuco dyes of the present invention.
- the infrared absorber can be placed in the same layer as the leuco dye as part of an admixture, or can be in a separate layer.
- the infrared absorber can be admixed with or in thermal contact with the leuco dye.
- the infrared absorber can be applied to the substrate in a separate adjacent layer prior to or after applying the leuco dyes as a layer to form a color forming composition on the substrate.
- consideration can also be given to choosing the infrared absorber such that any light absorbed in the visible range does not adversely affect the graphic display or appearance of the color forming composition either before or after development.
- the infrared absorber typically can be an organic compound, such as, but not limited to polymethine dyes such as pyrimidinetrione-cyclopentylidenes, guaiazulenyl dyes, croconium dyes, polymethine indolium dyes, metal complex IR dyes, cyanine, dyes indocyanine green, squarylium dyes, chalcogenopyryloarylidene dyes, metal thiolate complex dyes, bis(chalcogenopyrylo)polymethine dyes, oxyindolizine dyes, bis(aminoaryl)polymethine dyes, merocyanine dyes, indolizine dyes, pyrylium dyes, quinoid dyes, quinone dyes, phthalocyanine dyes, naphthalocyanine
- polymethine dyes such as pyrimidinetrione-cyclopentylidenes, guaia
- the infrared absorber can be polymethine dye or derivative thereof such as pyrimidinetrione-cyclopentylidene, squarylium dyes such as guaiazulenyl dyes, croconium dyes, or mixtures thereof.
- Suitable pyrimidinetrione-cyclopentylidene infrared absorbers include, for example 2,4,6(1H,3H,5H)-pyrimidinetrione 5-[2,5-bis[(1,3-dihydro-1,1,3-dimethyl-2H-indol-2-ylidene)ethylidene]cyclopentylidene]-1,3-dimethyl-(9CI) (SO322 available from Few Chemicals, Germany) shown in Formula I as follows:
- R1 and R2 can be aryl or alkyl chains with terminal hydroxyl or carboxyl substituents, aryl or substituted aryl such as naphthyl, indolenyl and quilonyl groups.
- Suitable squarylium dyes include, without limitation, cyclobutenediylium 1,3-bis[3,8-dimethyl-5-(1-methylethyl)-1-azulenyl]-2,4-dihdyroxy bis(inner salt) (9CI) (guaiazulenyl dye) having the chemical structure shown in Formula IV as follows:
- Croconium dyes have also shown suitable properties for use in conjunction with the present invention and have the general chemical structure shown in Formula V as follows:
- R1, R2, R3, and R4 can independently be methyl, one or more nitrogen, sulfur, aryl or alkyl chains including chains having terminal hydroxyl or carboxyl substituents, aryl or substituted aryl such as napthyl, indolenyl and quilonyl groups, or R1-R2 and/or R3-R4 can form a cyclic member having five or six carbons.
- Suitable polymethyl indolium compounds available from Aldrich Chemical Company that can be used include 2-[2-[2-chloro-3-[2-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-ethylidene]-1-cyclopenten-1-yl-ethenyl]-1,3,3-trimethyl-3H-indolium perchlorate; 2-[2-[2-Chloro-3-[2-(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)-ethylidene]-1-cyclopenten-1-yl-ethenyl]-1,3,3-trimethyl-3H-indolium chloride; 2-[2-[2-chloro-3-[(1,3-dihydro-3,3-dimethyl-1-propyl-2H-indol-2-ylidene)ethylidene]-1-cyclohexen-1-yl]ethen
- activators and absorbers discussed herein are typically separate compounds, such activity can also be provided by constituent groups of a binder and/or leuco dye which incorporates the activation and/or radiation absorbing action with the leuco dye and is considered within the scope of the present invention.
- the infrared absorber can be present in the color forming composition in an amount of from about 0.001 wt % to about 10 wt %, and typically, from about 0.5 wt % to about 1 wt %, although other weight ranges may be desirable depending on the activity of the particular absorber. These weight percentages represent an amount of infrared absorber that can be present when admixed with the leuco dye. These weight percentages can be altered in other embodiments, such as when the infrared absorber is applied in a separate layer of the color forming composition.
- the color forming composition typically includes at least a leuco dye, infrared absorber, and at least one of a stabilizer and an anti-fade agent as a single phase mixture
- the infrared absorber and/or stabilizer can alternatively be included in a separate layer from the leuco dye.
- a stabilizer can be included in the color forming composition.
- the stabilizer can be configured for stabilizing the infrared absorber, thus maintaining the activity of the infrared absorber sufficient to cause development of the leuco dye up to the time of development.
- the stabilizer can be in optical proximity with the infrared absorber.
- the stabilizers of the present invention can also be used in the stabilization of leuco dyes.
- One factor to consider in selection of infrared absorbers is the solubility of the absorber in a particular color forming composition. Infrared absorbers having solubility properties such that there is intimate contact between the color-forming components can be used.
- the color forming compositions of the present invention can be a single phase admixture of leuco dyes, infrared absorber, and stabilizer or can include each of the aforementioned components in separate layers.
- the stabilizer can be admixed with the infrared absorber in an overcoating over the leuco dye or in a layer formed as an overcoat over the infrared absorber.
- the addition of appropriate stabilizers aids in preventing non-infrared radiation, e.g., sunlight, fluorescent light, or UV radiation during UV cure, from disabling the infrared absorber prior to development using an infrared radiation source.
- stabilizers can aid in preventing undesirable changes in optical density of the color forming composition which may occur due to unintended development of the leuco dye either before or after development using an infrared radiation source.
- suitable stabilizers can include chromans, thiolane-nickel complexes, spiroindanes, and mixtures thereof.
- the stabilizer can be chroman having the chemical structure shown in Formula VI as follows:
- thiolane-nickel complexes such as bis(4-dimethylaminodithiobenzil) nickel and the related class having the general structure shown in Formula VII as follows:
- R1 and R2 can also be independently selected from methyl, substituted alkyl, aryl, heterocyclic aromatic groups with one nitrogen and one or more sulfur atoms in the ring, and tetrabutyl phosphonium (SP-4-1)-bis[4,5-di(mercapto- ⁇ S)-1,3-dithiole-2-thionato(2-)]nickelate(1-) (9CI) having the chemical structure shown in Formula VIII as follows:
- spiroindane stabilizers can be advantageously used in the compositions and methods of the present invention.
- suitable spiroindane stabilizers include 1,1′-spirobi[1H-indene]-5,5′,6,6′-tetrol-2,2′,3,3′-tetrahydro-3,3,3′,3′-tetramethyl-(9CI) having the chemical structure shown in Formula IX as follows:
- infrared absorber and stabilizer combinations have been found to be particularly effective.
- nickel complexes can be used to effectively stabilize croconium dyes, while having a limited stabilizing effect on indocyanine dyes.
- the chroman identified by Formula VI was found to be very effective with indocyanine dyes and croconium dyes.
- the chroman and thiolane-nickel complexes can be used to stabilize infrared absorbers such as pyrimidinetrione-cyclopentylidenes and squarylium dyes such as guaiazulenyl dye.
- thiolane-nickel complexes can be used to stabilize croconium infrared absorbers.
- chroman can be used to stabilize polymethyl indolium infrared absorbers.
- the stabilizers of the present invention can stabilize undeveloped portions of the color forming composition sufficient to retain activity of the infrared absorber over a period of at least 3 years. Additionally, the activity of the infrared absorber can be such that development of the color forming composition can occur in less than about 1 millisecond using a 50 mW infrared laser.
- One method of measuring the effectiveness of the particular stabilizer for use with specific infrared absorbers is to measure the optical density of a portion of the color forming composition applied on a substrate either before or after development using an infrared radiation source.
- the color forming composition can then be exposed to intense light, e.g., a 21K lux fluorescent light bank in a light chamber maintained at constant temperature, which simulates extended exposure to ambient light sources.
- the optical density can then be measured again and the change in optical density recorded.
- the stabilizers can effectively stabilize infrared absorbers over a period of at least three years such that no more than a 30% change in optical density is recorded. In most cases, the stabilizers of the present invention result in no more than about 25% degradation in optical density at 780 nm for infrared absorbers, or less than 0.1 OD units change in background optical density over a simulated three year period.
- the proportion of stabilizer in the color-forming composition can vary from composition to composition, and generally corresponds to the amount of infrared absorber used.
- the stabilizer can be present in the color forming composition, whether formed as an admixture or in separate layers, from about 0.1 wt % to about 10 wt %, and can also range from about 0.1 wt % to about 5 wt %.
- an anti-fade agent can be admixed with the leuco dye.
- Suitable anti-fade agents can be configured for inhibiting fading or oxidation of the leuco dye and/or other components of the color forming composition.
- anti-fading agents can be used, an effective class of compounds found to reduce browning and help reduce fading is anti-oxidants. Without subscribing to any particular theory, oxidation of the leuco dye is thought to be at least one cause of undesirable browning of the color forming composition both before and after development of the leuco dye.
- the anti-fade agent has the beneficial affect of similarly protecting other components from browning, e.g., the binder, infrared absorber, etc.
- the anti-fade agent can be chroman, vitamin E, vitamin E analogs such as vitamin E succinate and succinate esters of long chain alcohols, astaxanthin, ascorbic acid, carotene, and mixtures thereof.
- the anti-fade agent can be chroman, vitamin E, vitamin E analogs, astaxanthin, and mixtures thereof.
- chroman has proven useful as both an anti-fade agent and a stabilizer.
- other suitable stabilizers can be added to protect the infrared absorber.
- chroman if chroman is admixed with the leuco dye for use as an anti-fade agent, and an overcoat layer contains the infrared absorber, then the chroman would be limited, if not completely ineffective, in stabilizing the infrared absorber.
- a separate stabilizer can be admixed with the infrared absorber or overcoated thereon.
- chroman can be admixed with a leuco dye and an infrared absorber in a single phase mixture such that the chroman acts as both a stabilizer and an anti-fade agent.
- the anti-fade agent can reduce oxidation and browning effects such that developed and undeveloped portions of the color forming composition maintain substantially the same optical density over a time period of at least three years, unless specifically developed using infrared radiation as discussed in more detail below.
- a similar test of optical density can be used as described above in connection with the stabilizers to test the anti-browning properties of specific anti-fade agents in the color forming compositions of the present invention.
- the anti-fade agents of the present invention can prevent optical density changes greater than about 20% over a simulated three year period, and often reduce browning such that a change in optical density measures less than about 10%.
- the anti-fade agents of the present invention can be used with a number of leuco dyes as discussed above, however in one embodiment these anti-fade agents can be used with fluoran leuco dyes.
- the proportion of the anti-fade agent can vary depending on the leuco dye and associated components. However, the anti-fade agent can typically be present in the color forming composition in from about 0.1wt % to about 10.0 wt % of the color forming composition, and can also range from about 1.0 wt % to about 5.0 wt %.
- the color forming compositions of the present invention can also include various additional components such as colorants, liquid vehicles, and other additives known to those skilled in the art.
- the color forming composition can optionally include a reducing agent.
- Typical reducing agents include 1-phenyl-3-pyrozolidone (phenidone), hydrazine, formamide, formic acid, hexaarylbiimidazoles (HABI), ascorbic acid, phenols and substituted phenols, e.g., hydroquinone, and mixtures thereof.
- the color forming compositions of the present invention can have less than about 10 wt % of solids, which typically provides good coating properties.
- the solids content of a spin-coatable color forming composition can be from about 5 wt % to about 9 wt %.
- the color forming composition can also include a binder.
- Various binders can influence the development properties of the color forming composition such as development speed, light stability, and wavelengths which can be used to develop the composition.
- Suitable binders can include, but are not limited to, polymeric materials such as polyacrylate from monomers and oligomers, polyvinyl alcohols, polyvinyl pyrrolidines, polyethylenes, polyphenols or polyphenolic esters, polyurethanes, acrylic polymers, and mixtures thereof.
- the following binders can be used in the color forming composition of the present invention: cellulose acetate butyrate, ethyl acetate butyrate, polymethyl methacrylate, polyvinyl butyral, and mixtures thereof.
- Specific binders can be used for dissolving and/or dispersing the leuco dye, infrared absorber, and other components.
- Acceptable binder materials may also include, by way of example, UV curable polymers such as acrylate derivatives, oligomers, and monomers, such as included as part of a photo package.
- a photo package can include a light absorbing species that may be sensitized for curing using UV or electron beam curing systems. In choosing an appropriate binder, it is typically desirable to choose a binder which can be cured by radiation that does not also cause a color change in the leuco dye or otherwise decrease the stability of the color forming composition.
- Plasticizers can be either solid or liquid plasticizers. Such suitable plasticizers are well known to those skilled in the art, as exemplified in U.S. Pat. No. 3,658,543, which is incorporated herein by reference in its entirety. If the leuco dye and/or infrared absorber is applied in multiple layers, the plasticizer and binder can be included in any of the individual liquid carriers used to apply each layer.
- the colorants can be leuco dyes which are developed at non-infrared wavelengths or non-leuco colorants which can provide a background color.
- optional colorants can be standard pigments and/or dyes.
- the use of an opacifier pigment or other colorant can be used to provide background color to the substrate.
- the optional colorants can be added to the color forming composition, underprinted, or overprinted, as long as the development of the leuco dye is not prevented from at least some development due to the presence of the optional colorant and does not significantly reduce the activity of the stabilizer and/or anti-fade agent.
- portions of the leuco dye can then be developed producing an image with a colored background.
- opacifiers include calcium carbonate, titanium dioxide, and the like. If a colored background is desired that will remain independent of leuco dye development, an opacifier pigment, other pigment, and/or dye can be admixed in the carrier to impart the desired color, or can be applied as a separate coating.
- the color forming composition can be prepared in solution which is substantially transparent or translucent. Any suitable liquid carrier, e.g., an alcohol with a surfactant, can be used which is compatible with a particular leuco dye and/or other components chosen for use.
- a suitable liquid carrier e.g., an alcohol with a surfactant
- the optional colored coating produces a background color that can be visible underneath the solution layer.
- This colored coating can contain various colorants such as other pigments and/or dyes. Alteratively, an optional colorant may be added to the data layer to produce the desired background color.
- such coatings and compositions can be applied to the substrate using any of a variety of known techniques such as screen-printing, spin coating, sputtering, or spray coating. Each coating may be applied and then dried sequentially. In addition, such colored coatings may be applied over the color forming compositions of the present invention.
- lubricants such as lubricants, surfactants, and materials imparting moisture resistance
- materials imparting moisture resistance can also be added to provide mechanical protection to the color forming composition.
- overcoat compositions can also be used and are well known to those skilled in the art.
- the color forming composition can be applied to a substrate.
- the composition can be applied using any known technique such as spin-coating, screen printing, sputtering, spray coating, ink-jetting, or the like.
- substrates can be used such as optical disks, polymeric surfaces, glass, ceramics, or cellulose papers.
- the color forming composition can be applied to an optical disk and select portions thereof developed using an infrared laser or other infrared radiation source.
- an image to be formed on the surface can be digitally stored and then rasterized or spiralized.
- the resulting data can be delivered to an infrared radiation source which exposes portions of the color forming composition to infrared radiation while the optical disk is spinning.
- the infrared radiation source can be a 780 nm laser such as those found in commercially available CD/DVD writeable and/or rewriteable systems.
- the present invention relates generally to forming color images on a substrate using the color forming compositions of the present invention which can optionally be spin-coatable or printable.
- the compositions of the present invention can be prepared and applied in a variety of ways to a variety of substratres.
- a color forming composition can be prepared that includes a liquid carrier, which can be substantially removed upon drying, that contains, without limitation, a leuco dye, an infrared absorber, and at least one of a stabilizer and an anti-fade agent.
- the color forming composition can include a liquid carrier, which can act to improve coating performance, but which can be removed upon coating through known liquid removal processes. Typically, at least a portion of the liquid carrier can be driven off or allowed to evaporate after the coating process is complete.
- the liquid carrier can include, but is not limited to, solvents such as methylethyl ketone, isopropyl alcohol or other alcohols and diols, water, surfactants, and mixtures thereof.
- the color forming composition can cover the entire surface of a substrate or merely a portion thereof.
- an infrared absorber layer can be formed on at least approximately the same portions of the optical disk as a layer containing the leuco dye. This provides an optical disk having the infrared absorber layer in thermal contact with the leuco dye layer. If the two layers are not in actual contact, but are close enough in proximity for thermal activation of the leuco dye and/or activator to occur, the layers can also be said to be in thermal contact.
- the infrared absorber can be admixed with the leuco dye to form the color forming composition.
- the conditions under which the color forming compositions of the present invention are developed can be varied. For example, one can vary the infrared radiation wavelength, heat flux, and exposure time.
- the amount of heat which is to be applied depends partially on the activation energy of the development reaction of the leuco dye and the specific infrared absorber chosen. However, the heat applied is typically sufficient to develop the leuco dye without also decomposing the color forming composition or damaging the substrate. Such an energy level is typically well below the energy required for decomposition of the color forming composition. Variables such as spot size, focus, and laser power will also affect any particularly system design and can be chosen based on the desired results.
- the infrared radiation source can then direct infrared radiation to the color forming composition in accordance with the data received from a signal processor.
- leuco dye and/or infrared radiation absorber concentration and proximity to one another can also be varied to affect the development times and the optical density of the image formed.
- the infrared absorber and the leuco dye are present in a common layer, and thus, concentration ratios can be considered for a desired affect.
- concentration ratios can be considered for a desired affect.
- the leuco dye and infrared absorber are placed in separate layers, proximity can be considered.
- the color forming compositions of the present invention can be developed using lasers having from about 15 to 100 mW power usage, although lasers having a power outside this range can also be used. Typically, lasers having from about 30 mW to about 50 mW are readily commercially available and work well using the color forming composition described herein.
- the spot size can be determined by the infrared radiation that contacts the substrate at a single point in time.
- the spot size can be circular, oblong, or other geometric shape, and can range from about 1 to about 200 ⁇ m along a largest dimension, though smaller or larger sizes can also be used. In one embodiment, a radiation spot size of from about 10 ⁇ m to about 60 ⁇ m can be utilized.
- Heat flux is a variable that can be altered as well, and can be from about 0.05 to 5.0 J/cm 2 in one embodiment, and from about 0.3 to 0.5 J/cm 2 in a second embodiment.
- the color forming compositions of the present invention can be optimized by adjusting the concentrations and type of infrared absorber, leuco dye, and stabilizer and/or anti-fade agent. Heat flux in these ranges allow for development of leuco dyes in optimized compositions in from about 10 ⁇ sec to about 100 ⁇ sec per dot in some embodiments. Further, the color forming compositions of the present invention can be optimized for development in less than about 1 millisecond, such as from about 100 ⁇ sec to about 500 ⁇ sec.
- the color forming compositions can be optimized for development using infrared radiation having wavelengths of from about 760 nm to about 1250 nm, such as from about 760 nm to about 850 nm.
- the color forming compositions can be optimized for development using infrared radiation having a wavelength of from about 750 nm to about 900 nm.
- optimization for an infrared wavelength of about 780 nm can be done to utilize the present invention in commercially available lasers. Those skilled in the art can adjust these and other variables to achieve a variety of resolutions and developing times.
- the BK-400 lacquer dye was prepared by dissolving in 10% m-terphenyl at 170° C., cooling, and then grinding to a powder having particles sizes less than 5 micron), and then 1.9 g pure bisphenol-A (average particle size ⁇ 5 ⁇ m) was added.
- the mixture was rendered to a fine paste and screen printed onto a substrate at a thickness of approximately 7 ⁇ m to form an imaging medium.
- the coating on the medium was then UV cured by a mercury lamp.
- Direct marking was affected on the resulting coating substrate with a 45 mW laser. A mark of approximately 20 ⁇ m ⁇ 45 ⁇ m was produced with energy applications of about 20 ⁇ sec to 100 ⁇ sec. Direct marking occurs when the desired image is marked on the imaging medium, without the use of a printing intermediary.
- the infrared absorbance was determined using a spectrophotometer set to measure absorbance at 780 nm, and is reported as a OD (optical density) in Table 1 below:
- Example 2 The same procedure as in Example 1 was followed except that 20 g of active bipshenol-A and a specified amount of IR absorber and anti-fading agent were dissolved in the melted dibenzyl oxalate as indicated in Table 2 below:
Abstract
Description
2,4,6(1H,3H,5H)-pyrimidinetrione 5-[2,5-bis[(1,3-dihydro-1,1,3-trimethyl-2H-benz[e]indol-2-ylidene) ethylidene]cyclopentylidene]-1,3-dimethyl-(9CI) (Chemical Abstracts Services's 9th Collective Index) having the chemical structure shown in Formula II as follows:
or pyrimidinetrione-cyclopentylidenes having the chemical sub-structure shown in Formula III as follows:
where R1 and R2 can be aryl or alkyl chains with terminal hydroxyl or carboxyl substituents, aryl or substituted aryl such as naphthyl, indolenyl and quilonyl groups.
Croconium dyes have also shown suitable properties for use in conjunction with the present invention and have the general chemical structure shown in Formula V as follows:
where R1, R2, R3, and R4 can independently be methyl, one or more nitrogen, sulfur, aryl or alkyl chains including chains having terminal hydroxyl or carboxyl substituents, aryl or substituted aryl such as napthyl, indolenyl and quilonyl groups, or R1-R2 and/or R3-R4 can form a cyclic member having five or six carbons.
Other suitable stabilizers include thiolane-nickel complexes such as bis(4-dimethylaminodithiobenzil) nickel and the related class having the general structure shown in Formula VII as follows:
where R1 and R2 can also be independently selected from methyl, substituted alkyl, aryl, heterocyclic aromatic groups with one nitrogen and one or more sulfur atoms in the ring, and tetrabutyl phosphonium (SP-4-1)-bis[4,5-di(mercapto-ηS)-1,3-dithiole-2-thionato(2-)]nickelate(1-) (9CI) having the chemical structure shown in Formula VIII as follows:
Further, spiroindane stabilizers can be advantageously used in the compositions and methods of the present invention. Specific examples of suitable spiroindane stabilizers include 1,1′-spirobi[1H-indene]-5,5′,6,6′-tetrol-2,2′,3,3′-tetrahydro-3,3,3′,3′-tetramethyl-(9CI) having the chemical structure shown in Formula IX as follows:
or the corresponding isopropyl ether, 1,1′-spirobi[1H-indene]-2,2′,3,3′-tetrhaydro-3,3,3′,3′-tetramethyl-5,5′,6,6′-tetrapropoxy-(9CI) having the chemical structure shown in Formula X as follows:
Prior to addition, the BK-400 lacquer dye was prepared by dissolving in 10% m-terphenyl at 170° C., cooling, and then grinding to a powder having particles sizes less than 5 micron), and then 1.9 g pure bisphenol-A (average particle size<5 μm) was added. The mixture was rendered to a fine paste and screen printed onto a substrate at a thickness of approximately 7 μm to form an imaging medium. The coating on the medium was then UV cured by a mercury lamp.
TABLE 1 | |||||
Infrared | Initial | OD after | Change | Accept- | |
Absorber | Stabilizer | OD | Exposure | in OD | able |
IR780 | None | 0.9 | 0 | 0.9 | No |
IR780 | Chroman 1% | 4.5 | 0.6 | 3.9 | UV |
(Formula VI) | cure - | ||||
Yes | |||||
Light | |||||
fade - | |||||
No | |||||
IR780 | Nickel | 0.9 | 0 | 0.9 | No |
complex | |||||
(Formula XIII) | |||||
Sensient | None | 0.15 | 0 | 0.15 | No |
ST9/1 | |||||
(croconium) | |||||
Sensient | Nickel | 0.85 | 0.85 | 0 | Yes |
ST9/1 | complex 0.1% | ||||
(croconium) | (Formula XIII) | ||||
Sensient | Chroman 1% | 0.85 | 0.85 | 0 | Yes |
ST9/1 | (Formula VI) | ||||
(croconium) | |||||
S0322 | ST1207 | 0.75 | 0.75 | 0 | Yes |
(Formula I) | (Formula VII) | ||||
S0322 | Chroman 1% | 0.75 | 0.75 | 0 | Yes |
(Formula I) | (Formula VI) | ||||
TABLE 2 | |||||
Anti- | Ac- | ||||
Infrared | fading | Initial | OD after | Change | cept- |
Absorber | agent | OD | Exposure | in OD | able |
IR780 (0.2%) | None | 0.2 | 0.4 | 0.2 | No |
IR780 (0.2%) | Chroman 1% | 0.2 | 0.2 | 0 | Yes |
(Formula VI) | |||||
IR780 (0.2%) | Astaxanthine | 0.2 | 0.2 | 0 | Yes |
(9% solution | |||||
in fish oil) | |||||
Claims (51)
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US10/655,684 US7329630B2 (en) | 2003-09-05 | 2003-09-05 | Stabilizers and anti-fade agents for use in infrared sensitive leuco dye compositions |
TW093106501A TW200510498A (en) | 2003-09-05 | 2004-03-11 | Stabilizers and anti-fade agents for use in infrared sensitive leuco dye compositions |
PCT/US2004/028388 WO2005025883A1 (en) | 2003-09-05 | 2004-08-31 | Stabilizers and anti-fade agents for use in infrared sensitive leuco dye compositions |
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